WO2004111062A1 - Derives de la para-phenylenediamine comprenant un cycle diazacycloheptane substitue par un radical silyle, et leur utilisation pour colorer les fibres de keratine - Google Patents

Derives de la para-phenylenediamine comprenant un cycle diazacycloheptane substitue par un radical silyle, et leur utilisation pour colorer les fibres de keratine Download PDF

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Publication number
WO2004111062A1
WO2004111062A1 PCT/EP2004/007192 EP2004007192W WO2004111062A1 WO 2004111062 A1 WO2004111062 A1 WO 2004111062A1 EP 2004007192 W EP2004007192 W EP 2004007192W WO 2004111062 A1 WO2004111062 A1 WO 2004111062A1
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WIPO (PCT)
Prior art keywords
radical
trimethylsilyl
methyl
diazepan
phenylamine
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PCT/EP2004/007192
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English (en)
Inventor
Stéphane SABELLE
Madeleine Leduc
Laure Ramos
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L'oreal
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Publication of WO2004111062A1 publication Critical patent/WO2004111062A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the invention relates to para-phenylenediamine derivatives comprising a diazacycloheptane ring substituted with a silyl radical, and to their use for dyeing keratin fibres, and in ' particular ' uman keratin fibres such as the hair.
  • dye keratin fibres and in particular human keratin fibres - such as .the hair
  • dye compositions containing oxidation dye precursors in particular ortho- or para- phenylenediamines , ortho- or para-a inophenols , heterocyclic compounds such as diaminopyrazole • derivatives, pyrazolo [1, 5-a]p.yrimidine erivatives,, pyrimidine derivatives, pyridine derivatives, 5,6- , dihydroxyindole derivatives and 5, 6-dihy ' droxyindqli ⁇ e derivatives, which .are generally known as ' oxidation bases.
  • Oxidation dye precursors, or- oxidation bases, . are colourless or weakly coloured compounds that, when ' combined with oxidizing products, can give rise to coloured compounds or dyes by a process of. oxidative condensation. ;
  • the "permanent" coloration obtained with these oxidation dyes must moreover satisfy a certain- number, of requirements. Thus, it must have no toxicological drawbacks, it must allow shades to be obtained in the desired intensity, and ,it must show good resistance to external agents such as light, bad weather, washing, permanent-waving, perspiration, and rubbing ' . ' , • - ' ' . '
  • the dyes -must also allow white hairs to be covered and, .finally, they must, be -as unselective as possible, i.e..they must produce the. smallest possible colour differences along the same length of eratin- fibre, , which may -in " fact be differently, sensitized (i.e. damaged) ' between its end and its root. They must also show good chemical stability ⁇ in the formulations, • and must have a good toxicological profile. "
  • n is between Q and 4, it being understood that when n is greater than 1, then the radicals Ri may be identical ⁇ or different;
  • R 5 , R 6 and ,R 7 which -may be identical -or different, -represent: ' , •
  • - ' a carboxyalkyl radical; ' --. ' a carbamoyl radical; - ' a carbamoylalkyl ' -radical ; ' ..
  • alkyl radical which m ' ay ' be unsaturated; - a hydroxyalkyl' radical;
  • the present invention makes it possible- in ⁇ particular to obtain -chromatic,- strong, sparingly selective and. fast dyeing of- keratin fibres .
  • Another . subject of the invention is the use of- these- para-phenylenediamine . derivatives of formula- ' (I) to dye keratin -fibres,' and' in particular human keratin fibres such as ' the hair.
  • a subject of. the invention is- also a composition for -.dyeing keratin fibres, and. in ⁇ particular- ' human keratin.-- fibres such as the hair, comprising at least one para-phenylenediamine derivative of formula (I) , and also to the process for ' dyeing keratin fibres using this composition.
  • the derivatives of formula (I) are para- phenylenediamines' in which an amine is included in a ring of 1, 4-diazacycloheptane type, this ring also being referred to in the literature as 1, 4-diazepane.
  • alkyl radicals are linear or branched and comprise, unless otherwise indicated, from 1 to 10 carbon atoms and preferably ' from- 1 to 6 carbon atoms.
  • An alkoxy radical is an alkyl-0-radical, the alkyl radical being as defined, above .
  • unsaturated alkyl radical means an alkyl of 2 to 10 carbon atoms comprising one or more
  • dihydroxyethyl radical a l-hydroxy-2-aminoethyl radical; a l-amino-2-hydroxyethyl radical; a 1,2- diaminoethyl radical; a methoxy radical; an ethoxy radical; an allyloxy radical; a 2-hydroxyethyloxy radical.
  • the radical. Ri is chosen from an alkyl radical; a hydroxyalkyl radical; an aminoalkyl radical; an alkoxy radical; a hydroxyalkoxy radical.
  • the radical Ri may be a methyl radical; a hydroxymethyl radical; a 2-hydroxyethyl radical.; a 1,2- dihydroxyethyl radical; ⁇ a methoxy radical; a 2-hydroxy- ethoxy radical and more preferably a methyl- radical.; a hydroxymethyl radical; a 1, 2-dihydroxye hyl radical.
  • the oxidation bases of formula. (I) are such that n is equal, to 0.or 1. :
  • -the. radical. R 2 is. chosen from an alkyl . -• radical substituted with one or- two -trialkylsilyl radicals; an alkylaminoalkyl radical .substituted .with.a trialkylsilyl radical; ah alkylcarbamoylaminoalkyl radical' substituted- with a tri.alkyisilyl radical; an alkylcarbonyl a.dical .substituted with a- trialkylsilyl ' radical, which is it-self substituted with, a trialkylsilyl radical," an.
  • alkylcarbonyl radical substituted substituted ; with.a trialkylsilyl ' radical; an ' alkoxyalkyl radical substituted with a, trialkylsilyl; radical; .an alkyl- ' . carbonyl radical substituted with a dialkylphenylsilyl radical; an alkyl radical -substituted with a trialkylsilyl radical, which is itself substituted with a trialkylsilyl radical.
  • the radical R 2 may be a 3- (trimethylsilyl)propyl radical; a (trimethylsilyl) methyl radical; a 2- ⁇ [3- (trimethyl- silyi)propyl] amino ⁇ ethyl.
  • the radical -R 3 is chosen from a hydrogen- atom; - .a -hydroxyl- radical; an alkyl radical; a hydroxy- ' . alkyl radical;. an;.-amihoalkyl radical; a,carboxyl ' radical; ' an amino radical.
  • the .radical R 3 may be ' .a- hydrogen • atom; a hydroxyl : radical; ' .a carboxyl radical;. ' an- amino .radical; a hydroxymethyl radical; an aminom.ethyl,- radical, and more preferably- a hydrogen atom. '
  • the radical R 4 ' is chosen from an alkyl. radical;- a -hydroxyalkyl radical.; ' an .aminpalkyl radical'; ⁇ a .carboxyl..radical; a:• carbamoyi radical;- '•
  • the oxidation bases of formula (I) are such that m is equal to 0 or 1.
  • the ' compounds of formula (I) may be optionally salified with strong mineral acids, for instance HC1,. HBr or H 2 S0 4 , or organic acids, for instance acetic acid, lactic acid, tartaric acid, • citric acid or succinic acid.
  • strong mineral acids for instance HC1,. HBr or H 2 S0 4
  • organic acids for instance acetic acid, lactic acid, tartaric acid, • citric acid or succinic acid.
  • the carbon substituted with R 3 or R 4 may be of
  • a subject of the present invention is also the. use for the oxidation dyeing of keratin fibres, -and. in particular of human keratin fibres such as he hair,' of : a., para-phenylenediamine derivative ' of - formula .(I) as defined above..
  • composition for dyeing keratin fibres, and in -particular human keratin- fibres such .as the hair comprising, in ' a medium that is suitable for -dyeing,- at least one. para-phenylenediamine derivative of. - formula, ( ⁇ ) .
  • the . ' para-phenylenediamine, derivative (s)- .of- formula (I) is . are) each - generally present- in . an •- ⁇ amount of between 0.001% and 10% and preferably between ' 0.005% and ' 6% by weight approximately relative to the total weight of the dye composition.
  • the dye composition of the invention may contain one or more couplers conventionally used for dyeing keratin fibres .
  • couplers that may especially be mentioned are meta-pheny ' lenediamines, meta-aminophenols, meta-diphenols, naphthalene-based couplers and heterocyclic couplers, and the addition salts thereof.
  • Examples that may be mentioned include 2-methyl-5-aminophenol; 5-N- ( ⁇ -hydroxyethyl) ami-no- 2-methyl ⁇ henol-; .6-chlo.ro ⁇ 2-methyl-5-amino ⁇ henol; 3-aminophenol; 1, 3-dihydroxybenzene; 1, 3*-dihydroxy- 2-methylbenzene; 4-chloro-l, 3-dihydroxybenzene; 2, 4-diamino-l- ( ⁇ -hydroxyethyloxy) benzene; 2-amino- 4- ( ⁇ -hydroxyethylamino) -1-methoxybenzene; 1,3-diamin ⁇ - ' benzene; ⁇ ⁇ !
  • the coupler (s) is (are) each generally -present i ' an amount of between 0.001% and 10% by weight approximately relative to the total weight of the dye composition, and preferably between 0.005% and 6%.
  • the composition of the present invention may also comprise one or more additional oxidation bases conventionally used in oxidation dyeing., other than those described above.
  • these additional oxidation bases are chosen frompara- phenylenediamines other than the derivatives of formula (I), bis (phenyl) alkylenediamines, para-aminophenols, bis-para-aminophenols, ortho-aminophenols, ortho- phenylenediamihes, heterocyclic bases., and the addition salts thereof.
  • para-pheny ' lenediamines which can be mentioned, for example, are para-phenylenediamine;. para-tolylenediamine;' 2-chloro-para- ⁇ henylenediamine; 2 • 3-dimethy1-para-phenylenediamine ' ; 2, 6-dimethyl-para- ' phenyle ⁇ ediamine; ' 2 ' , 6-diethyl- ⁇ ara-phenyienediamine'; ⁇ 2, 5-dimethyl-para-phenylenediamine; N.,.N-dimethyl-para- ' phenylen ' ediamine; N,N- ' diethyl- ⁇ ara-phen ' yl ' enediamine; .
  • N. r N-dipropyl ' -para-phenylenediamine 4-amino-N,N- diethyl-3-methylaniline; ' N,N-bis ( ⁇ -hydroxyethyl) -para- phenylenediamine; 4- ⁇ N,N-bis ( ⁇ -hydroxyethyl) a ino- 2-methylaniline; 4-N,N-bis ( ⁇ -hydroxyethyl) amino- 2-chloroaniline; 2-.( ⁇ -hydroxyethyl) -para- -• . - ' " phenyle ' nediamine; ,2-fluoro-para-phehyle ' nediamine; ' .
  • para-phenylenediamines mentioned ' above are para-phenylenediamine; para-tolylenediamine; 2-isopropyl-para-phenylenediamine; 2- ( ⁇ -hydroxyethyl) - para-phenylenediamine; 2- ( ⁇ -hydroxyethyloxy) -para- phenylenediamine; 2, 6-dlmethyl-para-phenylenediamlrie; 2, 6-diethy!-pa ' ra-ph ' enylenediamine; 2, 3-dimethyl-para- phenylenediami ⁇ e; . N,N-bis ( ⁇ -hydfoxyethyl) -para-.
  • phenylenediamine - 2-chloro-para-phenylenediamine; . ' 2- ( ⁇ -acetylaminoethyloxy) -para-phenyleri . ediamine and the addition salts thereof with an acid are particularly, • preferred. ' ' . - - ' ⁇ ' .
  • para-aminophenols which can ⁇ be mentioned, for example, are para-aminophenol; 4-amino-. 3-methylphenol; 4-amino-3-fluorophenol; 4-amino- 3-hydroxymethylphehpl; 4-amino-2-methylphenol; 4-amino- 2-hydroxymethylphenol; 4-amin ' o-2-methoxymethylphenol; 4-amino ⁇ 2-aminomethylphenol; 4-amino-2- ( ⁇ -hydroxyethyl- aminomethyl)phenol; 4-amino.-2-fluorophenol, and the addition salts thereof with an . acid.
  • ortho-aminophenols that can be mentioned, .for example, are 2-aminophenol; 2-amino-5- methylphenol; 2-amino-6-methylphenol; 5-acetamido-2- aminop ' henol, and the addition salts thereof- with an. acid. ' . ' -, ' • - ' ' ⁇ Among the ' heterocyclic bases, .mention may be made, " , for example, -of- pyridirie derivatives,' pyrimidine ' . derivative ' s and pyrazole derivatives.
  • pyridine oxidation bases that are useful .in the present invention- are the 3-aminopyrazolo [1, 5-a] pyridine oxidation bases or the addition salts thereof described," for example, in patent application FR 2 801 308.
  • pyrazolo [1, 5-a] pyrid-3-ylamine 2-acetylaminopyrazolo [1, 5-a]pyrid-3-ylamine; 2-morpholin-4-ylpyrazolo [1, 5-a]pyrid-3-ylamine;- 3-aminopyrazolo [1, 5-a] pyridine-2-carboxylic acid; 2-methoxypyrazolo [1, 5-a]pyrid-3-ylamino; (3-aminopyrazolo [1, 5-a]pyrid-7-yl) ethanol; 2- (3-aminopyrazolo- [1, 5-a]pyrid-5-yl) ethanol; 2, 3-aminopyrazolo [
  • FR- -2 733 749 and DE 195 43 988 such as 4, 5-diamino-l-methylpyrazole; 4,5- diamino-1- ( ⁇ -hydroxyethyl)pyrazole; 3,4-diamino- pyrazole; 4, 5-diamino-l- (4' -chlorobenzyl) yrazole; ' 4,5- diamino-1, 3-dimethylpyrazole; 4, 5-diamino-3-methyl-l- phenylpyrazole; 4, 5-diamino-l-methyl-3-phenylpyrazole; 4-amino-l, 3-dimethyl-5-hydrazinopyrazole; l-benzyl-4, 5- diamino-3-methylpyrazole; 4, 5-diamino-3-tert-butyl- 1-methyl ⁇ yrazole;.
  • The- oxidation, base.(s) . present in the composition of the invention .is. (are) each ' generally- present in an amount of between- 0.0,01% and, 10% by weight approximately relative. to the. total weight'of ⁇ the dye composition, preferably between 0.005% and 6%..
  • bases " and-of the" couplers . ' .that may be used 'in the context of the invention are chosen especially from the addition salts with an acid, such as the hydrochlorides, hydrobromides, sulphates, citrates, succ ' iriates, ta ' rtrates, lactates, tosylates, benzenesulphonates, • phosphates and acetates, and the addition salts with a ' base, such as sodium hydroxide, - potassium hydroxide, ammonia, amines or alkanolamines .
  • an acid such as the hydrochlorides, hydrobromides, sulphates, citrates, succ ' iriates, ta ' rtrates, lactates, tosylates, benzenesulphonates, • phosphates and acetates
  • a ' base such as sodium hydroxide, - potassium hydroxide, ammonia,
  • the dye composition in accordance with the invention may also contain one ' or more direct dyes that may be chosen especially from nitrobenzene dyes, azo direct dyes and methine direct dyes . These direct dyes may be of nonionic, anionic or cationic -nature.
  • the medium that is suitable for dyeing is -a cosmetic medium that generally consists of water or a mixture of water and at least one organic solvent to dissolve the compounds, that would not be sufficiently- soluble in water.
  • organic .solvent mention may be made, for example, of'. C ⁇ -C 4 lower alkanols, such -as ethanol and isopropanol; : - polyols ' and polyol ethers such as 2-butoxyethanol, propylene " glycol, pr ⁇ pylene- glycol; monomethyl ether, . diethylene- .glycol monoethyl ether and monomethyl ether ' , as well as aromatic alcohols . such ' as -benzyl alcohol or phenoxyethanol, and. mixtures, thereof .
  • the solvents are preferably present- in proportions- preferably of. between ' 1% and.40% by Weight approximately, relative to the total weight' of the dye • ..composition, and ' even ' more preferably between .5% -and 30%. by weight approximately.
  • the dye composition in accordance with the invention can also contain various adjuvants conventionally used iri compositions for dyeing the hair, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers arrivingor mixtures thereof, inorganic or organic thickeners, and in particular anionic, cationic, nonionic or amphoteric associative polymeric , thickeners, antioxidants,' penetration agents, sequestering agents, fragrances, buffers-, dispersing agents, packaging agents such as, for example, silicones, which may or may not be volatile or modified, film-forming agents, ceramides,- preserving agents and opacifiers.
  • adjuvants conventionally used iri compositions for dyeing the hair such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic
  • the above adjuvants are' generally present in an amount for each- of them of betwee 0.01% and 20% by weight relative to the -weight ⁇ of the composition. .
  • The. pH of the dye composition in accordance. ' with -the ' invention- s generally - etween about 3 ' and 12' and preferabl .between about 5 and 11. It may be . adjusted to the desired value using acidifying or basifying agents usually used in the dyeing of keratin fibres, or ' alternatively using standard buffer systems.
  • acidifying agents that may .be mentioned, for example, are inorganic or organic acids such as hydrochloric ' acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tar ' taric acid, citric acid and lactic acid, and sulphonic acids.
  • inorganic or organic acids such as hydrochloric ' acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tar ' taric acid, citric acid and lactic acid, and sulphonic acids.
  • basifying agents hat may be mentioned, for example, are aqueous ammonia, . alkaline carbonates, alkanolamines such as mono-, di- and triethano-lamirve and derivatives thereof, sodium hydroxide, potassium hydroxide and the compounds of formula (II) below:
  • W is. a propylene residue that is- optionally ' - ' substituted with a hydroxyl group or a C ⁇ -C 4 alkyl-.. radical;
  • R a , Rb, R c and-Rd, . which may be identical, or different, represent a hydrogen atom, a ,C ⁇ -C 4 alkyl radical, or a C 1 -C 4 hydroxyalkyl. radical.
  • the dye composition according to the-,-. • invention may,be in -various forms, such as in .the form of liquids,, creams.,or gels, .or in any other form ' that ' is, .s ⁇ itable ⁇ -for, dyeing keratin fibres, and, especially- human hair .
  • the process of the ' present invention is a process in which the composition according to the present invention, as described above is applied to the fibres, and the colour is developed using an oxidizing agent.
  • the colour may be developed at acidic, neutral or alkaline pH and the oxidizing agent ' may be added to the composition of the invention just at the time of use, or it may be used ' starting with an oxidizing composition ' .containing it, which is applied simultaneously or sequentially to the composition of; the invention.
  • the composition according to the present invention is mixed, preferably at the time of use, with a composition containing, in a medium that is . suitable ' for .dyeing, ' at least one oxidizing agent, this - oxidizing -agent .being present in an amount ' that ' is. sufficient; ' , to ' develop a coloration.
  • an action time of 3-t ' o 50 "minutes approximately,' - preferably 5 to 30- minutes ' approximately,- the keratin . fibres are rinsed, washed with ' shampoo, . rinsed ' again - and then dried. • - ' -, -.
  • The, oxidizing agents conventionally used- " " for • the. ' oxidation dyeing of keratin fibres are,, for " ⁇ example, hydrogen-' peroxide, urea, peroxide, alkali-metal bromates, .persalts such as-- perborates- and pers-ulpha ' tes,, peracids and oxidase enzymes, among which mention, may be made of peroxidases, 2-electron oxidoreductases such as uricases, and .4-electron oxygenases . , for instance • laccases. Hydrogen peroxide is particularly preferred.
  • the oxidizing composition may also contain . various adjuvants conventionally used in compositions for dyeing the hair and as defined above.
  • the pH of the oxidizing composition containing the oxidizing agent is such .that, .after mixing with the dye composition, the pH of the resulting composition applied to the keratin fibres, ranges preferably between 3 and 12 approximately • and ⁇ even more preferably between 5 and 11. It may be adjusted to the desired value by means of acidifying or basifying agents -usually .used in the dyeing of keratin, fibres and as defined above.
  • the ready-to-use composition ' that- is finally .. applied to the ' keratin fibres may be in various- forms-, ' such .as - in the form of liquids, creams or : gels or any-' - other form that is suitable for -dyeing keratin • fibres ' , and especially/human hair-.
  • Another subject of the invention is a -multi- - compartment dyeing device or kit", in which a- first . - compartment contains the dye . composition of the present , invention defined above and a second compartment contains an. -oxidizing composition.
  • This device ; ay be- equipped with a. means- for applying the desired-mixture ' ,, to the hair, ' ' ' such as. the devices described'-in .patent ' . ' . FR-2 586 913 in the name of the Applicant.
  • this device uses this device to dye keratin fibres using a process that includes mixing- a dye composition comprising at least one oxidation base of formula (I) with an oxidizing agent and applying the mixture obtained to the keratin fibres for a time that is sufficient to develop 'the desired coloration.
  • reaction medium After filtering off the catalyst under nitrogen, the reaction medium is poured onto aqueous hydrochloric acid. The filtrate is evaporated to dryness under reduced pressure. After crystallization from isopropanol and drying at 40°C under vacuum and over potassium hydroxide, 1.53 g of white crystals are obtained, i.e-. a yield of 73%.
  • Pentasodium salt of diethylenetriamine- pentaacetic acid as an ' aqueous 4.0% ' solution ' ' .; '' '" ' 0. ' 48 g.A.M. C B -C I O alkyl polyglucoside as an aqueous
  • each ' composition is ' mixed with an equal weight of 2 .
  • 0-volumes aqueous hydrogen peroxide solution (6% by weight) . .
  • a final pH of 9.5 is obtained.
  • each ' composition is mixed with an equal weight of 20-volumes aqueous hydrogen peroxide solution (6% by weight) .
  • a final pH' of 7 is obtained.

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Abstract

L'invention porte sur des dérivés de la para-phénylènediamine de formule (I) contenant un cycle diazacycloheptane substitué par un radical silyle R, et sur leur utilisation pour colorer les fibres de kératine et en particulier les fibres de kératine humaines dont les cheveux. L'invention porte également sur une composition colorante pour fibres de kératine et en particulier les fibres de kératine humaines dont les cheveux, comprenant au moins un dérivé de la para-phénylènediamine contenant un cycle diazacycloheptane substitué par un radical silyle, et sur un procédé de coloration utilisant cette composition. L'invention permet d'obtenir une teinture chromatique, résistante, économique et rapide des fibres de kératine.
PCT/EP2004/007192 2003-06-13 2004-06-11 Derives de la para-phenylenediamine comprenant un cycle diazacycloheptane substitue par un radical silyle, et leur utilisation pour colorer les fibres de keratine WO2004111062A1 (fr)

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FR0307165 2003-06-13
FR0307165A FR2856059B1 (fr) 2003-06-13 2003-06-13 Derives de para-phenylenediamine comportant un cycle diazacycloheptane substitue par un radical silyle pour la teinture des fibres keratiniques

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2828488A1 (fr) * 2001-08-08 2003-02-14 Oreal Composition pour la teinture de fibres keratiniques contenant une paraphenylenediamine substituee par un radical diazacycloheptane

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2828488A1 (fr) * 2001-08-08 2003-02-14 Oreal Composition pour la teinture de fibres keratiniques contenant une paraphenylenediamine substituee par un radical diazacycloheptane

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